The literature on the diversification of the higher education workforce has tended to focus on broad brush changes to patterns of employment and working conditions. What has been less remarked is ways in which individuals are negotiating the structures and stretching the parameters within which they work, including experience outside higher education. Thus, academic work is also seen in the context of broader opportunities, for instance extended networks that enable individuals to construct new forms of professional capital. Arising from these conditions, two empirical studies, on which this paper draws, demonstrate the emergence of what might be termed itinerant identities. The triggers for these are seen as arising, on the one hand, from a spirit of exploration, that is an intrinsic interest in entering new areas of activity, and, on the other, from a desire for a greater sense of security by keeping a range of options open. The two motivations are not mutually exclusive and are likely to depend on individual circumstances and career stages. It would also appear that, in space outside higher education, individuals may find some of the freedom and autonomy they may feel that they have lost as a result of increased structural requirements including, for instance, workload models and performance assessment.